Alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetamides and their use as herbicides

ABSTRACT

The invention relates to novel alkyl sulphinyl and alkyl sulphonyl-1,2,4-thiadiazolyloxy acetamides of formula (I) ##STR1## in which n is the numbers 1 or 2, 
     R 1  is hydrogen or possibly substituted alkyl, alkenyl, alkinyl or aralkyl, 
     R 2  is possibly substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy or alkinyloxy, or 
     R 1  and R 2  together with the nitrogen atom to which they are bound form a possibly substituted, saturated or unsaturated nitrogen heterocycle which may contain other hetero atoms and to which a benzo group may be annellated, and 
     R 3  is possibly substituted alkyl, aryl or arylalkyl, 
     and also processes and novel intermediate products for producing the novel compounds and their use as herbicides.

The invention relates to novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides, to processes and novel intermediates for their preparation and to their use as herbicides.

It has already been disclosed that certain alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides, for example N-isopropyl-α-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide, exhibit herbicidal properties (cf., for example, EP-A 348 737 and the preceding, but not prepublished, Patent Application German Patent Specification 4 317 323 of 25.5.1993). However, the activity of these previously disclosed compounds is not completely satisfactory in all areas of application, particularly at low application rates and concentrations.

The novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiaazolyloxyacetamides of the general formula (I) have now been found, ##STR2## in which n represents the numbers 1 or 2,

R¹ represents hydrogen or represents alkyl, alkenyl, alkinyl or aralkyl which are in each case optionally substituted,

R² represents alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy or alkinyloxy which are in each case optionally substituted, or

R¹ and R², together with the nitrogen atom to which they are bonded, form an optionally substituted, saturated or unsaturated nitrogen heterocycle which can contain additional heteroatoms and to which a benzo grouping can be fused, and

R³ represents alkyl, aryl or arylalkyl which are in each case optionally substituted,

where the compounds N-isopropyl-α-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide, N-isopropyl-α-(3-methylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide, N-isopropyl-α-(3-ethylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide, N-iso-propyl-α-(3 -ethylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide, N-isopropyl-α-(3-propylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide, N-isopropyl-α-(3-propylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide--cf. EP-A 348 737--and also the compounds N-methyl-N-(4-fluoro-phenyl)-α-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide,N-methyl-N-(4-fluoro-phenyl)-α-(3-methylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide,N-methyl-N-(4-fluoro-phenyl)-α-(3-ethylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide,N-ethyl-N-(4-fluoro-phenyl)-α-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide,N-ethyl-N-(4-fluoro-phenyl)-α-(3-methylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide and N-ethyl-N-(4-fluoro-phenyl)-α-(3-ethylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-acetamide--cf. German Patent Specification 4 317 323 of 25.5.1993--are excepted by disclaimer.

In addition, it has been found that the novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides of the general formula (I) are obtained if

(a) 1,2,4-thiadiazole derivatives of the general formula (II) ##STR3## in which x represents halogen or the grouping --S(O)_(n) --R³, and

n and R³ have the abovementioned meaning,

are reacted with hydroxyacetamides of the general formula (III) ##STR4## in which R¹ and R² have the abovementioned meaning,

where appropriate in the presence of a diluent, where appropriate in the presence of an acid-binding agent and where appropriate in the presence of a catalyst, or if

(b) alkyl(aryl-, aralkyl-)thio-1,2,4-thiadiazolyloxyacetamides of the general formula (IV) ##STR5## in which R¹, R² and R³ have the abovementioned meaning,

are reacted with an oxidizing agent, where appropriate in the presence of a catalyst and where appropriate in the presence of a diluent.

Finally, it has been found that the novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides of the general formula (I) possess interesting herbicidal properties.

While in some cases exhibiting very good tolerability with regard to cultivated plants, for example cotton, the novel compounds of the formula (I) surprisngly exhibit a substantially more powerful effect against weeds which are difficult to control than does the chemically similar, known compound N-isopropyl-α-(3-methylsulphinyl-1,2,4-thiadiazol-5-yl-oxy)-acetanilide.

The invention preferably relates to compounds of the formula (I) in which

n represents the numbers 1 or 2,

R¹ represents hydrogen or C₁ -C₈ -alkyl (which is optionally substituted by fluorine, chlorine, cyano or C₁ -C₄ -alkoxy), represents C₂ -C₈ -alkenyl (which is optionally substituted by fluorine and/or chlorine), represents C₂ -C₈ -alkinyl or represents benzyl,

R² represents C₁ -C₈ -alkyl (which is optionally substituted by fluorine, chlorine, cyano or C₁ -C₄ -alkoxy), or C₂ -C₈ -alkenyl (which is optionally substituted by fluorine and/or chlorine), represents C₂ -C₈ -alkinyl, represents C₃ -C₆ -cycloalkyl (which is optionally substituted by chlorine and/or C₁ -C₃ -alkyl), represents C₅ -or C₆ -cycloalkenyl, represents benzyl (which is optionally substituted by fluorine, chlorine and/or C₁ -C₄ -alkyl), represents phenyl (which is optionally substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkylthio), represents C₁ -C₈ -alkoxy (which is optionally substituted by C₁ -C₄ -alkoxy), or represents C₃ -C₄ -alkenyloxy, or

R¹ and R², together with the nitrogen atom to which they are bonded, form a saturated or unsaturated, five- to seven-membered nitrogen heterocycle which is optionally substituted once to three times by C₁ -C₃ -alkyl and which is optionally benzo fused, and

R³ represents C₁ -C₈ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy, dioxolanyl or dioxanyl) or represents phenyl or phenyl-C₁ -C₂ -alkyl (which are in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy),

with the exception of the compounds which are excepted above by disclaimer.

The invention relates, in particular, to compounds of the formula (I) in which

n represents the numbers 1 or 2,

R¹ represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or n-, i- or s-pentyl (which are in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy), or represents propenyl, butenyl, propinyl or butinyl,

R² represents methyl, ethyl, n- or i-propyl, n-, i or s-butyl, n-, i- or s-pentyl, or n-, i- or s-hexyl (which are in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy), represents propenyl, butenyl, pentenyl, propinyl, butinyl or pentinyl, represents cyclopentyl or cyclohexyl (which are in each case optionally substituted by methyl and/or ethyl), represents cyclohexenyl, represents benzyl (which is optionally substituted by fluorine, chlorine and/or methyl) or represents phenyl (which is in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy or ethoxy), or represents methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, or n-, i- or s-pentyloxy (which are in each case optionally substituted by methoxy or ethoxy), or

R¹ and R², together with the nitrogen atom to which they are bonded, represent piperidinyl which is optionally substituted one to three times by methyl and/or ethyl, represent pyrrolidinyl which is optionally substituted once or twice by methyl and/or ethyl, represent perhydroazepinyl or represent 1,2,3,4-tetrahydro(iso)-quinolinyl, and

R³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl (which are in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy) or represents phenyl or benzyl (which are in each case optionally substituted by fluorine, chlorine, cyano, methyl or methoxy),

with the exception of the compounds which are excepted above by disclaimer.

Examples of the possible meanings of the grouping ##STR6## in the formula (I) are listed in the following Table 1.

                  TABLE 1                                                          ______________________________________                                         Examples of the meaning of the grouping                                         ##STR7##                                                                       ##STR8##                                                                                         ##STR9##                                                    ______________________________________                                         N(CH.sub.3).sub.2 N(C.sub.4 H.sub.9).sub.2                                     N(C.sub.2 H.sub.5).sub.2                                                                         N(CH.sub.2 CHCH.sub.2).sub.2                                 N(C.sub.3 H.sub.7).sub.2                                                                         N(CH.sub.2 CCH).sub.2                                         ##STR10##                                                                                        ##STR11##                                                    ##STR12##                                                                                        ##STR13##                                                    ##STR14##                                                                                        ##STR15##                                                    ##STR16##                                                                                        ##STR17##                                                    ##STR18##                                                                                        ##STR19##                                                    ##STR20##                                                                                        ##STR21##                                                    ##STR22##                                                                                        ##STR23##                                                    ##STR24##                                                                                        ##STR25##                                                    ##STR26##                                                                                        ##STR27##                                                    ##STR28##                                                                                        ##STR29##                                                    ##STR30##                                                                                        ##STR31##                                                    ##STR32##                                                                                        ##STR33##                                                    ##STR34##                                                                                        ##STR35##                                                    ##STR36##                                                                                        ##STR37##                                                    ##STR38##                                                                                        ##STR39##                                                    ##STR40##                                                                                        ##STR41##                                                    ##STR42##                                                                                        ##STR43##                                                    ##STR44##                                                                                        ##STR45##                                                    ##STR46##                                                                                        ##STR47##                                                    ##STR48##                                                                                        ##STR49##                                                    ##STR50##                                                                                        ##STR51##                                                    ##STR52##                                                                                        ##STR53##                                                    ##STR54##                                                                                        ##STR55##                                                    ##STR56##                                                                                        ##STR57##                                                    ##STR58##                                                                                        ##STR59##                                                    ##STR60##                                                                                        ##STR61##                                                    ##STR62##                                                                                        ##STR63##                                                    ##STR64##                                                                                        ##STR65##                                                    ##STR66##                                                                                        ##STR67##                                                    ##STR68##                                                                                        ##STR69##                                                    ##STR70##                                                                                        ##STR71##                                                    ##STR72##                                                                                        ##STR73##                                                    ##STR74##                                                                                        ##STR75##                                                    ##STR76##                                                                                        ##STR77##                                                    ##STR78##                                                                                        ##STR79##                                                    ##STR80##                                                                                        ##STR81##                                                    ##STR82##                                                                                        ##STR83##                                                    ##STR84##                                                                                        ##STR85##                                                    ##STR86##                                                                                        ##STR87##                                                    ##STR88##                                                                                        ##STR89##                                                    ##STR90##        N(CH.sub.2 CH.sub.2 CN).sub.2                                 ##STR91##                                                                                        ##STR92##                                                    ##STR93##                                                                                        ##STR94##                                                    ##STR95##                                                                                        ##STR96##                                                    ##STR97##                                                                                        ##STR98##                                                    ##STR99##                                                                                        ##STR100##                                                   ##STR101##                                                                                       ##STR102##                                                   ##STR103##                                                                                       ##STR104##                                                   ##STR105##                                                                                       ##STR106##                                                   ##STR107##                                                                                       ##STR108##                                                   ##STR109##                                                                    ______________________________________                                    

The above-listed general radical definitions, or those given in preference ranges, apply both to the end products of the formula (I) and, correspondingly, to the starting compounds or intermediates which are in each case required for the preparation.

These radical definitions may be arbitrarily combined among themselves, that is also between the given ranges of preferred compounds.

If, for example, 3-methylsulphinyl-5-chloro-1,2,4-thiadiazole and N-methyl-hydroxyacetanilide are used as starting compounds, the course of the reaction in the novel process (a) can then be outlined by the following formula scheme: ##STR110##

If, for example, N-cyclohexyl-N-methyl-α-(3-methylthio-1,2,4-thiadiazol-5-yl-oxy)-acetamide and hydrogen peroxide are used as starting compounds, the course of the reaction in the novel process (b) can then be outlined by the following formula scheme: ##STR111##

The 1,2,4-thiadiazole derivatives which are to be used as starting compounds in the novel process (a) for preparing the compounds of the general formula (I) are defined generally by the formula (II). In the formula (II), n and R³ preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for n and R³.

With the exception of the compounds 5-chloro-3-methylsulphonyl-1,2,4-thiadiazole and 3,5-bis-methylsulphonyl-1,2,4-thiadiazole (cf. Chem. Ber. 97 (1964), 225-237; German Published Specification 1544505), the starting compounds of the formula (II) are still not disclosed in the literature and, with the exception of the abovementioned compounds, are likewise part of the subject-matter of the present application.

The 1,2,4-thiadiazole derivatives of the formula (II) are obtained if corresponding alkylthio compounds of the formula (V) ##STR112## in which R³ and X have the abovementioned meaning,

are reacted with an oxidizing agent, for example hydrogen peroxide, where appropriate in the presence of a reaction auxiliary, for example sodium tungstate or sulphuric acid, and where appropriate in the presence of a diluent, for example water, methanol, formic acid and/or acetic acid, at temperatures of between 0° C. and 150° C. (cf. the preparation examples).

The precursors of the formula (V) are known and/or may be prepared by processes which are known per se (cf. Chem. Ber. 90 (1957), 892-901; loc. cit. 97 (1964), 225-237; East German Patent Specification 221060; preparation examples)

The hydroxyacetamides which are additionally to be used as starting compounds in the novel process (a) for preparing compounds of the formula (I) are defined generally by the formula (III).

In formula (III), R¹ and R² preferably or in particular have those meanings which have already been indicated above, in connection with the description of the novel compounds of the formula (I), as being preferably or particularly preferred for R¹ and R².

The hydroxyacetamides of the formula (III) are known and/or may be prepared by processes which are known per se (cf. U.S. Pat. No. 4509971 and U.S. Pat. No. 4645525; and, in addition, U.S. Pat. No. 4334073, DE-OS (German Published Specification) 3038598, DE-OS (German Published Specification) 3038636, EP-A 37526, EP-A 348737 and DE-OS (German Published Specification) 3819477.

The alkyl(aryl-, aralkyl-)thio-1,2,4-thiadiazolyloxyacetamides to be used as starting compounds in the novel process (b) for preparing the compounds of the general formula (I) are defined generally by the formula (IV). In the formula (IV), R¹, R² and R³ preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for R¹, R² and R³.

The starting compounds of the formula (IV) are known and/or may be prepared by processes which are known per se (cf. EP-A 018497 and EP-A 029171).

The novel process (a) for preparing the novel alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides of the formula (I) is preferably carried out using diluents. These diluents preferably include hydrocarbons, for example toluene, xylene or cyclohexane, halogeno hydrocarbons, for example methylene chloride, ethylene chloride, chloroform or chlorobenzene, ethers, for example diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, diisobutyl ether, glycol dimethyl ether, tetrahydrofuran and dioxane, alcohols, for example methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol or tert-butanol, ketones, for example acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, for example methyl acetate and ethyl acetate, amides, for example dimethyl formamide, dimethylacetamide and N-methyl-pyrrolidone, nitrites, for example acetonitrile and propionitrile, sulphoxides, for example dimethyl sulphoxide, and also water or aqueous salt solutions.

In this context, the salts which are used are preferably chlorides or sulphates of alkali metals or alkaline earth metals, for example sodium chloride, potassium chloride or calcium chloride. Sodium chloride is particularly preferred.

The novel process (a) is advantageously carried out using acid-binding agents. Those which are preferably used are strongly basic alkali metal and alkaline earth metal compounds, for example oxides, for example sodium, potassium, magnesium and calcium oxide, hydroxides, for example sodium, potassium, magnesium and calcium hydroxide, alkoxides, for example sodium and potassium tert-butoxide, and/or carbonates, for example sodium, potassium, magnesium and calcium carbonate.

The addition of from 0.01 to 10% by weight (based on the glycolamide of the formula (III) which is employed) of a phase transfer catalyst may be found to be advantageous in some cases. Examples of such catalysts which may be mentioned are:

Tetrabutylammonium chloride, tetrabutylammonium bromide, tributyl-methylphosphonium bromide, trimethyl-C₁₃ /C₅ -alkyl-ammonium chloride, dibenzyl-dimethylammonium methylsulphate, dimethyl-C₁₂ /C₁₄ -alkyl-benzylammonium chloride, tetrabutylammonium hydroxide, 18-crown-6, triethylbenzylammonium chloride, trimethylbenzylammonium chloride and tetraethylammonium bromide.

In the novel process (a), the reaction temperatures may be varied over a relatively wide range. In general, the process is carried out at temperatures of between -50° C. and +110° C., preferably at temperatures of between -20° C. and +80° C.

In general, the novel process (a) is carried out under standard pressure; however, it can also be carried out under elevated or reduced pressure, between approximately 0.1 and 10 bar.

In general, in order to carry out the novel process (a), from 0.5 to 5 mol, preferably from 0.8 to 1.5 mol, of hydroxyacetamide of the formula (III) are employed per mol of 1,2,4-thiadiazole derivative of the formula (II). The reaction components may be added together in any sequence. In each case, the reaction mixture is stirred until the reaction is complete, and working-up takes place in accordance with customary methods (cf. the preparation examples).

The novel process (b) for preparing the compounds of the formula (I) is carried out using an oxidizing agent. The customary chemicals which are suitable for oxidizing organic sulphides (thioethers) to corresponding sulphoxides or sulphones are suitable for use in this context. Examples of suitable oxidizing agents which may be mentioned are: hydrogen peroxide (H₂ O₂), performic acid, peracetic acid, perpropionic acid, perbenzoic acid and 3-chloro-perbenzoic acid, and chlorine or hypochlorous acid and its alkali metal or alkaline earth metal salts.

The novel process (b) is optionally carried out in the presence of a catalyst. Salts of metals of the IVth, Vth and VIth subgroup of the periodic system of the elements are preferably used as catalysts in this context. Examples of these catalysts which may be mentioned are sodium (meta)vanadate, sodium molybdate and sodium tungstate.

The novel process (b) is preferably carried out using a diluent. The organic solvents which are customary for oxidation reactions are, together with water, suitable for use as diluents in this context. These solvents preferably include chlorinated hydrocarbons, such as methylene chloride, ethylene chloride, chloroform, tetrachloromethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene, alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and sec-butanol, and carboxylic acids, such as formic acid, acetic acid and propionic acid.

In the novel process (b), the reaction temperatures may be varied over a relatively wide range. In general, the process is carried out at temperatures of between -20° C. and +60° C., preferably at temperatures of between 0° C. and 40° C.

In general, the novel process (b) is carried out under standard pressure. However, it is also possible to carry it out under elevated or reduced pressure--in general between 0.1 bar and 10 bar.

In general, in order to carry out the novel process (b), between 1 and 10 mol, preferably between 1 and 5 mol, of oxidizing agent and, where appropriate, between 0.001 and 0.1 mol, preferably between 0.01 and 0.05 mol, of a catalyst, are employed per 1 mol of starting compound of the formula (II).

In a preferred embodiment of the novel process (b), the starting compound of the formula (II) and, where appropriate a catalyst are initially introduced into a diluent, and the oxidizing agent is slowly metered in while stirring. The reaction mixture is stirred until the reaction is complete and is then worked up in a customary manner (cf. the preparation examples).

The novel active compounds can be used as defoliants, desiccants, haulm killers and, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the novel compounds act as total or selective herbicides depends essentially on the amount used.

The novel active compounds can be used, for example, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the novel active compounds is in no way restricted to these genera, but also extends in the same manner to other plants.

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial terrain and rail tracks and on paths and areas with or without tree stands. Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pastures, and for selective weed control in annual crops.

The novel compounds of the formula (I) are suitable, in particular, for selectively controlling monocotyledenous and dicotyledonous weeds in dicotyledonous cultures, especially in the pre-emergence process.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixing the novel active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifiers and/or dispersants and/or foam-formers.

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolyzates; suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the novel active compounds, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Suitable herbicides for the mixtures are known herbicides, for example anilides such as, for example, diflufenican and propanil; arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines such as, for example, oryzalin, pendimethalin and trifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as, for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet; sulphonylureas such as, for example, amidosulphuron, bensulphuron-methyl, chlorimuron-ethyl, chlorsulphuron, cinosulphuron, metsulphuron-methyl, nicosulphuron, primisulphuron, pyrazosulphuron-ethyl, thifensulphuron-methyl, triasulphuron and tribenuron-methyl; thiocarbamates such as, for example, butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulphocarb, thiobencarb and triallate; triazines such as, for example, atrazine, cyanazine, simazine, simetryn, terbutryn and terbutylazine; triazinones such as, for example, hexazinone, metamitron and metribuzin; others such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufo-sinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

A mixture with other known novel active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil conditioners, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or spreading.

The novel active compounds can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the rates of application are between 10 g and 10 kg of active compound per hectare of soil surface, preferably between 50 g and 5 kg per ha.

The preparation and use of the novel active compounds can be seen from the examples which follow.

PREPARATION EXAMPLES Example 1 ##STR113## 3.6 g (15 mmol) of 3,5-bis-methylsulphonyl-1,2,4-thiadiazole are dissolved, together with 2.6 g (15 mmol) of hydroxyaceto-2-ethyl-piperidide, in 40 ml of acetone. A solution of 0.6 g of sodium hydroxide in 3.3 ml of water is added dropwise to this at -20° C. The reaction mixture is stirred at -15° C. for 12 hours. It is then diluted to twice its volume with water and the whole is shaken with chloroform. The organic phase is separated off, dried with sodium sulphate and filtered. The solvent is carefully distilled off from the filtrate under a water pump vacuum.

4.8 g (77% of theory) of α-(3-methylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-aceto-2-ethyl-piperidide are obtained as an oily residue with a refracted index N_(D) ²⁰ =1.5329.

Example 2 ##STR114## 29.5 g (0.10 mol) of α-(3-methylthio-1,2,4-thiadiazol-5-yl-oxy)-aceto-N-methyl-anilide are dissolved in 50 ml of methylene chloride. After 100 ml of water has been added, 17.75 g (0.25 mol) of chlorine are passed in, while stirring, within the space of approximately 3 hours. The organic phase is then separated off, washed with water, dried with sodium sulphate and filtered. The solvent is distilled off from the filtrate under a water pump vacuum and the residue is stirred up with a little methanol; the crystalline product is isolated by filtering it off with suction.

7.0 g (21% of theory) of α-(3-methylsulphonyl-1,2,4-thiadiazol-5-yl-oxy)-aceto-N-methyl-anilide are obtained with a melting point of 82° C.

The compound of the formula (I) which are listed in the following Table 2 may also, for example, be prepared in analogy with Preparation Examples 1 and 2 and in accordance with the general description of the novel preparation processes.

                                      TABLE 2                                      __________________________________________________________________________     Examples of the compounds of the formula (I)                                   R.sup.1        R.sup.2                 Physical                                Ex. No.                                                                            n                                                                                 ##STR115##         R.sup.3      data                                    __________________________________________________________________________     3   2 CH.sub.3                                                                                 ##STR116##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5455                 4   2                                                                                 ##STR117##         CH.sub.3     n.sub.D.sup.20 = 1.5738                 5   2 CH(CH.sub.3).sub.2                                                                      OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                       CH.sub.3     n.sub.D.sup.20 = 1.5001                 6   2 CH.sub.3                                                                                 ##STR118##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5556                 7   2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         CH.sub.3     n.sub.D.sup.20 = 1.5142                 8   2                                                                                 ##STR119##         CH.sub.3     n.sub.D.sup.20 = 1.5359                 9   2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       CH.sub.3     n.sub.D.sup.20 = 1.5370                 10  2 CH(CH.sub.3).sub.2                                                                       ##STR120##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5370                 11  2 CH(CH.sub.3).sub.2                                                                      OCH(CH.sub.3).sub.2                                                                       CH.sub.3     n.sub.D.sup.20 = 1.5038                 12  2 CH(CH.sub.3).sub.2                                                                       ##STR121##                                                                               CH.sub.3     m.p.: 70° C.                     13  2 CH(CH.sub.3).sub.2                                                                       ##STR122##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5470                 14  2 CH.sub.3                                                                                 ##STR123##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5090                 15  2 CH.sub.3 CH.sub.2 OCH.sub.3                                                                        CH.sub.3     n.sub.D.sup.20 = 1.5270                 16  2                                                                                 ##STR124##         CH.sub.3     n.sub.D.sup.20 = 1.5445                 17  2 CH.sub.3                                                                                 ##STR125##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5648                 18  2                                                                                 ##STR126##         CH.sub.3                                             19  2 CH.sub.3                                                                                 ##STR127##                                                                               CH.sub.3                                             20  2                                                                                 ##STR128##         CH.sub.3     n.sub.D.sup.20 = 1.5260                 21  2 CH.sub.3                                                                                 ##STR129##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5305                 22  2 CH.sub.3                                                                                 ##STR130##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5732                 23  2 CH.sub.3                                                                                 ##STR131##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5520                 24  2 CH.sub.3                                                                                 ##STR132##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5563                 25  2 CH(CH.sub.3).sub.2                                                                       ##STR133##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5312                 26  2 CH(CH.sub.3).sub.2                                                                       ##STR134##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5385                 27  2 CH.sub.3                                                                                 ##STR135##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5519                 28  2                                                                                 ##STR136##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5269                 29  2                                                                                 ##STR137##         C.sub.2 H.sub.5                                                                             m.p.: 84° C.                     30  2                                                                                 ##STR138##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5058                 31  2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5208                 32  2                                                                                 ##STR139##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5319                 33  2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             m.p.: 73° C.                     34  2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5070                 35  2                                                                                 ##STR140##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5311                 36  2 CH.sub.3                                                                                 ##STR141##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5359                 37  2 CH.sub.3                                                                                 ##STR142##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5490                 38  2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5130                 39  2 CH(CH.sub.3).sub.2                                                                      OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                       C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5008                 40  2 CH(CH.sub.3).sub.2                                                                       ##STR143##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5249                 41  2 CH(CH.sub.3).sub.2                                                                       ##STR144##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5441                 42  2 CH(CH.sub.3).sub.2                                                                       ##STR145##                                                                               C.sub.2 H.sub.5                                                                             m.p.: 96° C.                     43  1                                                                                 ##STR146##         CH.sub.3     n.sub.D.sup.20 = 1.5475                 44  1                                                                                 ##STR147##                                                                             OCH.sub.3  CH.sub.3     n.sub.D.sup.20 = 1.5262                 45  1 CH.sub.3                                                                                 ##STR148##                                                                               CH.sub.3                                             46  1 CH(CH.sub.3).sub.2                                                                       ##STR149##                                                                               CH.sub.3                                             47  1                                                                                 ##STR150##         CH.sub.3     n.sub.D.sup.20 = 1.5553                 48  1                                                                                 ##STR151##                                                                             OCH.sub.3  CH.sub.3     n.sub.D.sup.20 = 1.5104                 49  1 CH.sub.3                                                                                 ##STR152##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5648                 50  2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           CH.sub.3     n.sub.D.sup.20 = 1.5108                 51  2 CH.sub.3                                                                                 ##STR153##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5577                 52  2 CH.sub.3                                                                                 ##STR154##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5334                 53  2 CH.sub.3                                                                                 ##STR155##                                                                               n-C.sub.3 H.sub.7                                                                           m.p.: 79° C.                     54  2                                                                                 ##STR156##         n-C.sub.3 H.sub.7                                    55  2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           n-C.sub.3 H.sub.7                                                                           m.p.: 73° C.                     56  2                                                                                 ##STR157##         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5176                 57  2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5129                 58  2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                         n-C.sub.3 H.sub.7                                                                           m.p.: 61° C.                     59  2                                                                                 ##STR158##         n-C.sub.3 H.sub.7                                    60  2                                                                                 ##STR159##         n-C.sub.3 H.sub.7                                    61  2 C.sub.2 H.sub.5                                                                          ##STR160##                                                                               n-C.sub.3 H.sub.7                                    62  2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5043                 63  2                                                                                 ##STR161##         n-C.sub.3 H.sub.7                                    64  2 CH.sub.3                                                                                 ##STR162##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5401                 65  2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5067                 66  2 CH.sub.3                                                                                 ##STR163##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5121                 67  2                                                                                 ##STR164##         n-C.sub.3 H.sub.7                                    68  2 i-C.sub.3 H.sub.7                                                                        ##STR165##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5256                 69  2 i-C.sub.3 H.sub.7                                                                        ##STR166##                                                                               n-C.sub.3 H.sub.7                                    70  2 i-C.sub.3 H.sub.7                                                                        ##STR167##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5231                 71  2 i-C.sub.3 H.sub.7                                                                        ##STR168##                                                                               n-C.sub.3 H.sub.7                                    72  2 CH.sub.3                                                                                 ##STR169##                                                                               n-C.sub.3 H.sub.7                                    73  2 CH.sub.3                                                                                 ##STR170##                                                                               n-C.sub.3 H.sub.7                                    74  2 CH.sub.3                                                                                 ##STR171##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5399                 75  2 CH.sub.3                                                                                 ##STR172##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5311                 76  2 CH.sub.3                                                                                 ##STR173##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5303                 77  2                                                                                 ##STR174##         n-C.sub.4 H.sub.9                                    78  2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           n-C.sub.4 H.sub.9                                                                           m.p.: 84° C.                     79  2                                                                                 ##STR175##         n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5189                 80  2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5262                 81  2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                         n-C.sub.4 H.sub.9                                                                           m.p.: 55° C.                     82  2                                                                                 ##STR176##         n-C.sub.4 H.sub.9                                    83  2                                                                                 ##STR177##         n-C.sub.4 H.sub.9                                    84  2 C.sub.2 H.sub.5                                                                          ##STR178##                                                                               n-C.sub.4 H.sub.9                                    85  2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                         n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5021                 86  2                                                                                 ##STR179##         n-C.sub.4 H.sub.9                                    87  2 CH.sub.3                                                                                 ##STR180##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5120                 88  2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.4824                 89  2 CH.sub.3                                                                                 ##STR181##                                                                               n-C.sub.4 H.sub.9                                    90  2                                                                                 ##STR182##         n-C.sub.4 H.sub.9                                    91  2 i-C.sub.3 H.sub.7                                                                        ##STR183##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5062                 92  2 i-C.sub.3 H.sub.7                                                                        ##STR184##                                                                               n-C.sub.4 H.sub.9                                    93  2 i-C.sub.3 H.sub.7                                                                        ##STR185##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5128                 94  2 i-C.sub.3 H.sub.7                                                                        ##STR186##                                                                               n-C.sub.4 H.sub.9                                    95  2 CH.sub.3                                                                                 ##STR187##                                                                               n-C.sub.4 H.sub.9                                    96  2 CH.sub.3                                                                                 ##STR188##                                                                               n-C.sub.4 H.sub.9                                    97  2 CH.sub.3                                                                                 ##STR189##                                                                               i-C.sub.3 H.sub.7                                    98  2 CH.sub.3                                                                                 ##STR190##                                                                               i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5435                 99  2 CH.sub.3                                                                                 ##STR191##                                                                               i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5447                 100 2                                                                                 ##STR192##         i-C.sub.3 H.sub.7                                    101 2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           i-C.sub.3 H.sub.7                                    102 2                                                                                 ##STR193##         i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5185                 103 2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5252                 104 2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                         i-C.sub.3 H.sub.7                                    105 2                                                                                 ##STR194##         i-C.sub.3 H.sub.7                                    106 2                                                                                 ##STR195##         i-C.sub.3 H.sub.7                                    107 2 C.sub.2 H.sub.5                                                                          ##STR196##                                                                               i-C.sub.3 H.sub.7                                    108 2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                         i-C.sub.3 H.sub.7                                    109 2                                                                                 ##STR197##         i-C.sub.3 H.sub.7                                    110 2 CH.sub.3                                                                                 ##STR198##                                                                               i-C.sub.3 H.sub.7                                    111 2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         i-C.sub.3 H.sub.7                                    112 2 CH.sub.3                                                                                 ##STR199##                                                                               i-C.sub.3 H.sub.7                                    113 2                                                                                 ##STR200##         i-C.sub.3 H.sub.7                                    114 2 i-C.sub.3 H.sub.7                                                                        ##STR201##                                                                               i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5374                 115 2 i-C.sub.3 H.sub.7                                                                        ##STR202##                                                                               i-C.sub.3 H.sub.7                                    116 2 i-C.sub.3 H.sub.7                                                                        ##STR203##                                                                               i-C.sub.3 H.sub.7                                                                           m.p: 89° C.                      117 2 i-C.sub.3 H.sub.7                                                                        ##STR204##                                                                               i-C.sub.3 H.sub.7                                    118 2 CH.sub.3                                                                                 ##STR205##                                                                               i-C.sub.3 H.sub.7                                    119 2 CH.sub.3                                                                                 ##STR206##                                                                               i-C.sub.3 H.sub.7                                    120 2 CH.sub.3                                                                                 ##STR207##                                                                               i-C.sub.3 H.sub.7                                    121 2 CH.sub.3                                                                                 ##STR208##                                                                               i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5341                 122 2 CH.sub.3                                                                                 ##STR209##                                                                               n-C.sub.3 H.sub.7                                    123 2 CH.sub.3                                                                                 ##STR210##                                                                               n-C.sub.3 H.sub.7                                    124 2 CH.sub.3                                                                                 ##STR211##                                                                               n-C.sub.4 H.sub.9                                    125 2 CH.sub.3                                                                                 ##STR212##                                                                               n-C.sub.4 H.sub.9                                    126 2 CH.sub.3                                                                                 ##STR213##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   127 2 CH.sub.3                                                                                 ##STR214##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   128 2 C.sub.2 H.sub.5                                                                          ##STR215##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   129 2 CH.sub.3                                                                                 ##STR216##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                          n.sub.D.sup.20 = 1.5400                 130 2 i-C.sub.3 H.sub.7                                                                        ##STR217##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   131 2 i-C.sub.3 H.sub.7                                                                        ##STR218##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   132 2 i-C.sub.3 H.sub.7                                                                        ##STR219##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   133 2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   134 2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                         CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   135 2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   136 2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                         CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   137 2                                                                                 ##STR220##         CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   138 2                                                                                 ##STR221##         CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   139 2                                                                                 ##STR222##         CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   140 2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   141 2 CH.sub.3                                                                                 ##STR223##                                                                               CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   142 2 CH.sub.3                                                                                 ##STR224##                                                                                ##STR225##                                          143 2 CH.sub.3                                                                                 ##STR226##                                                                                ##STR227##                                          144 2 C.sub.2 H.sub.5                                                                          ##STR228##                                                                                ##STR229##                                          145 2 CH.sub.3                                                                                 ##STR230##                                                                                ##STR231##                                          146 2 i-C.sub.3 H.sub.7                                                                        ##STR232##                                                                                ##STR233##                                          147 2 i-C.sub.3 H.sub.7                                                                        ##STR234##                                                                                ##STR235##                                          148 2 i-C.sub.3 H.sub.7                                                                        ##STR236##                                                                                ##STR237##                                          149 2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                            ##STR238##                                          150 2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                          ##STR239##                                          151 2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                        ##STR240##                                          152 2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                          ##STR241##                                          153 2                                                                                 ##STR242##                                                                                         ##STR243##                                          154 2                                                                                 ##STR244##                                                                                         ##STR245##                                          155 2                                                                                 ##STR246##                                                                                         ##STR247##                                          156 2 CH.sub.3 n-C.sub.4 H.sub.9                                                                          ##STR248##                                          157 2 CH.sub.3                                                                                 ##STR249##                                                                                ##STR250##                                          158 2 CH.sub.3                                                                                 ##STR251##                                                                                ##STR252##                                          159 2 CH.sub.3                                                                                 ##STR253##                                                                                ##STR254##                                          160 2 C.sub.2 H.sub.5                                                                          ##STR255##                                                                                ##STR256##                                          161 2 CH.sub.3                                                                                 ##STR257##                                                                                ##STR258##  m.p.: 127° C.                    162 2 i-C.sub.3 H.sub.7                                                                        ##STR259##                                                                                ##STR260##                                          163 2 i-C.sub.3 H.sub.7                                                                        ##STR261##                                                                                ##STR262##                                          164 2 i-C.sub.3 H.sub.7                                                                        ##STR263##                                                                                ##STR264##                                          165 2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                            ##STR265##                                          166 2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                          ##STR266##                                          167 2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                        ##STR267##                                          168 2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                          ##STR268##                                          169 2                                                                                 ##STR269##                                                                                         ##STR270##                                          170 2                                                                                 ##STR271##                                                                                         ##STR272##                                          171 2                                                                                 ##STR273##                                                                                         ##STR274##                                          172 2 CH.sub.3 n-C.sub.4 H.sub.9                                                                          ##STR275##                                          173 2 CH.sub.3                                                                                 ##STR276##                                                                                ##STR277##                                          174 2 CH.sub.3                                                                                 ##STR278##                                                                                ##STR279##                                          175 2 CH.sub.3                                                                                 ##STR280##                                                                                ##STR281##                                          176 2 C.sub.2 H.sub.5                                                                          ##STR282##                                                                                ##STR283##                                          177 2 CH.sub.3                                                                                 ##STR284##                                                                                ##STR285##                                          178 2 i-C.sub.3 H.sub.7                                                                        ##STR286##                                                                                ##STR287##                                          179 2 i-C.sub.3 H.sub.7                                                                        ##STR288##                                                                                ##STR289##                                          180 2 i-C.sub.3 H.sub.7                                                                        ##STR290##                                                                                ##STR291##                                          181 2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                            ##STR292##                                          182 2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                          ##STR293##                                          183 2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                        ##STR294##                                          184 2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                          ##STR295##                                          185 2                                                                                 ##STR296##                                                                                         ##STR297##                                          186 2                                                                                 ##STR298##                                                                                         ##STR299##                                          187 2                                                                                 ##STR300##                                                                                         ##STR301##                                          188 2 CH.sub.3 n-C.sub.4 H.sub.9                                                                          ##STR302##                                          189 2 CH.sub.3                                                                                 ##STR303##                                                                                ##STR304##                                          190 2 CH.sub.3 CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5192                 191 2 CH.sub.3 CH(CH.sub.3).sub.2                                                                        CH.sub.3     n.sub.D.sup.20 = 1.5075                 192 2 CH(CH.sub.3).sub.2                                                                       ##STR305##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5603                 193 2 CH.sub.3                                                                                 ##STR306##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5440                 194 2 CH(CH.sub.3).sub.2                                                                       ##STR307##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5362                 195 2 CH.sub.3                                                                                 ##STR308##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5230                 196 2 CH.sub.3                                                                                 ##STR309##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5402                 197 2                                                                                 ##STR310##         n-C.sub.3 H.sub.7                                                                           m.p.: 112° C.                    198 2                                                                                 ##STR311##         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5192                 199 2                                                                                 ##STR312##         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5122                 200 2 CH.sub.3                                                                                 ##STR313##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5306                 201 2 CH(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.4853                 202 2 CH(CH.sub.3).sub.2                                                                       ##STR314##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5299                 203 2 CH.sub.3                                                                                 ##STR315##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5351                 204 2 C.sub.2 H.sub.5                                                                          ##STR316##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5084                 205 2                                                                                 ##STR317##         n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5148                 206 2                                                                                 ##STR318##         n-C.sub.4 H.sub.9                                                                           m.p.: 121° C.                    207 2 CH.sub.3                                                                                 ##STR319##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5245                 208 2                                                                                 ##STR320##         n-C.sub.4 H.sub.9                                                                           m.p.: 85° C.                     209 2 CH.sub.3                                                                                 ##STR321##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5148                 210 2 CH(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                         n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.4908                 211 2 CH(CH.sub.3).sub.2                                                                       ##STR322##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5251                 212 2 CH.sub.3                                                                                 ##STR323##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5309                 213 2 C.sub.2 H.sub.5                                                                          ##STR324##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5287                 214 2 C.sub.2 H.sub.5                                                                          ##STR325##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5287                 215 2 C.sub.2 H.sub.5                                                                         n-C.sub.4 H.sub.9                                                                         CH.sub.3     m.p.: 56° C.                     216 2 C.sub.2 H.sub.5                                                                         n-C.sub.4 H.sub.9                                                                         C.sub.2 H.sub.5                                                                             m.p.: 68° C.                     217 2 n-C.sub.3 H.sub.7                                                                        ##STR326##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5419                 218 2 CH.sub.3                                                                                 ##STR327##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5485                 219 2                                                                                 ##STR328##         i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5246                 220 2 CH.sub.3                                                                                 ##STR329##                                                                               i-C.sub.3 H.sub.7                                                                           m.p.: 120° C.                    221 2                                                                                 ##STR330##         i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5208                 222 2 C.sub.2 H.sub.5                                                                          ##STR331##                                                                               i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5328                 223 2 CH.sub.3                                                                                 ##STR332##                                                                               i-C.sub.4 H.sub.9                                                                           m.p.: 70° C.                     224 2                                                                                 ##STR333##         i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.4965                 225 2 CH.sub.3                                                                                 ##STR334##                                                                               i-C.sub.4 H.sub.9                                                                           m.p.: 68° C.                     226 2                                                                                 ##STR335##         i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.4963                 227 2                                                                                 ##STR336##         i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.4992                 228 2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5136                 229 2 CH(CH.sub.3).sub.2                                                                       ##STR337##                                                                               i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5248                 230 2 CH(CH.sub.3).sub.2                                                                       ##STR338##                                                                               i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5212                 231 2 CH.sub.3                                                                                 ##STR339##                                                                               i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5243                 232 2 C.sub.2 H.sub.5                                                                          ##STR340##                                                                               i-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5243                 233 2 CH.sub.3                                                                                 ##STR341##                                                                                ##STR342##  m.p.: 117° C.                    234 2 CH.sub.3                                                                                 ##STR343##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5561                 235 2 C.sub.2 H.sub.5                                                                         n-C.sub.4 H.sub.9                                                                         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5089                 236 2 n-C.sub.3 H.sub.7                                                                        ##STR344##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5416                 237 2 C.sub.2 H.sub.5                                                                         n-C.sub.4 H.sub.9                                                                         C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            n.sub.D.sup.20 = 1.5033                 238 2                                                                                 ##STR345##         C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            n.sub.D.sup.20 = 1.5072                 239 2 CH.sub.3                                                                                 ##STR346##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            n.sub.D.sup.20 = 1.5154                 240 2 CH.sub.3                                                                                 ##STR347##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            m.p.: 68° C.                     241 2 n-C.sub.3 H.sub.7                                                                        ##STR348##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            n.sub.D.sup.20 = 1.5306                 242 2                                                                                 ##STR349##         C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            n.sub.D.sup.20 = 1.5579                 243 2 CH.sub.3                                                                                 ##STR350##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            m.p.: 54° C.                     244 2 CH.sub.3                                                                                 ##STR351##                                                                               n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5289                 245 2 i-C.sub.4 H.sub.9                                                                        ##STR352##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5387                 246 2 i-C.sub.4 H.sub.9                                                                        ##STR353##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5465                 247 2                                                                                 ##STR354##         CH.sub.3     n.sub.D.sup.20 = 1.5272                 248 2                                                                                 ##STR355##         CH.sub.3     n.sub.D.sup.20 = 1.5331                 249 2 CH.sub.3                                                                                 ##STR356##                                                                               CH.sub.3     m.p.: 223° C.                    250 2 CH.sub.3 CH.sub.2 C.sub.6 H.sub.5                                                                  CH.sub.3     n.sub.D.sup.20 = 1.5425                 251 2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                         CH.sub.3     m.p.: 56° C.                     252 2 CH(CH.sub.3).sub.2                                                                       ##STR357##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5436                 253 2 CH(CH.sub.3).sub.2                                                                       ##STR358##                                                                               CH.sub.3     Fp.: 72° C.                      254 2 CH(CH.sub.3).sub.2                                                                       ##STR359##                                                                               CH.sub.3     m.p.: 91° C.                     255 2 CH(CH.sub.3).sub.2                                                                       ##STR360##                                                                               CH.sub.3     m.p.: 87° C.                     256 2 CH(CH.sub.3).sub.2                                                                       ##STR361##                                                                               CH.sub.3     m.p.: 115° C.                    257 2 CH(CH.sub.3).sub.2                                                                       ##STR362##                                                                               CH.sub.3     m.p.: 98° C.                     258 2 CH(CH.sub.3).sub.2                                                                       ##STR363##                                                                               CH.sub.3     m.p.: 86° C.                     259 2 C.sub.2 H.sub.4 OCH.sub.3                                                               C.sub.2 H.sub.4 OCH.sub.3                                                                 CH.sub.3     n.sub.D.sup.20 = 1.5133                 260 2                                                                                 ##STR364##         CH.sub.3     n.sub.D.sup.20 = 1.5175                 261 2 C.sub.2 H.sub.5                                                                          ##STR365##                                                                               CH.sub.3     m.p: 73° C.                      262 2                                                                                 ##STR366##         CH.sub.3     n.sub.D.sup.20 = 1.5338                 263 2 CH.sub.3 CH.sub.2 CF.sub.3                                                                         CH.sub.3     m.p.: 123° C.                    264 2 CH.sub.3                                                                                 ##STR367##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5617                 265 2 CH.sub.3                                                                                 ##STR368##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5187                 266 2 OCH.sub.3                                                                                ##STR369##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5096                 267 2                                                                                 ##STR370##         CH.sub.3     m.p.: 80° C.                     268 2 i-C.sub.3 H.sub.7                                                                        ##STR371##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5496                 269 2 i-C.sub.3 H.sub.7                                                                        ##STR372##                                                                               CH.sub.3     m.p.: 74° C.                     270 2 i-C.sub.3 H.sub.7                                                                        ##STR373##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5392                 271 2 i-C.sub.3 H.sub.7                                                                        ##STR374##                                                                               CH.sub.3     m.p.: 105° C.                    272 2 i-C.sub.3 H.sub.7                                                                        ##STR375##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5355                 273 2                                                                                 ##STR376##         CH.sub.3     n.sub.D.sup.20 = 1.5067                 274 2 i-C.sub.3 H.sub.7                                                                        ##STR377##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5415                 275 2                                                                                 ##STR378##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5308                 276 2 CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR379##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5599                 277 2 (CH.sub.2).sub.3 CH.sub.3                                                                ##STR380##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5493                 278 2 CH.sub.3                                                                                 ##STR381##                                                                               C.sub.2 H.sub.5                                                                             m.p.: 114° C.                    279 2                                                                                 ##STR382##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5366                 280 2 C.sub.2 H.sub.5                                                                          ##STR383##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5329                 281 2 CH.sub.3                                                                                 ##STR384##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5482                 282 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5113                 283 2 CH.sub.3 i-C.sub.3 H.sub.7                                                                         n-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5249                 284 2 CH.sub.3                                                                                 ##STR385##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5766                 285 2 CH.sub.3                                                                                 ##STR386##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5248                 286 2 OCH.sub.3                                                                                ##STR387##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5052                 287 2                                                                                 ##STR388##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5284                 288 2 i-C.sub.3 H.sub.7                                                                        ##STR389##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5461                 289 2 i-C.sub.3 H.sub.7                                                                        ##STR390##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5430                 290 2 i-C.sub.3 H.sub.7                                                                        ##STR391##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5367                 291 2 i-C.sub.3 H.sub.7                                                                        ##STR392##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5424                 292 2 i-C.sub.3 H.sub.7                                                                        ##STR393##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5354                 293 2 i-C.sub.3 H.sub.7                                                                       OCH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5066                 294 2 i-C.sub.3 H.sub.7                                                                        ##STR394##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5325                 295 2 i-C.sub.3 H.sub.7                                                                        ##STR395##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.4842                 296 2 i-C.sub.3 H.sub.7                                                                        ##STR396##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5384                 297 2 i-C.sub.3 H.sub.7                                                                        ##STR397##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5108                 298 2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5093                 299 2 CH.sub.3                                                                                 ##STR398##                                                                               (CH.sub.3).sub.2 CHCH.sub.2                                                                 m.p.: 67° C.                     300 2 i-C.sub.3 H.sub.7                                                                        ##STR399##                                                                               CH.sub.3     m.p.: 78° C.                     301 2 n-C.sub.4 H.sub.9                                                                       n-C.sub.4 H.sub.9                                                                         CH.sub.3     n.sub.D.sup.20 = 1.5284                 302 2                                                                                 ##STR400##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5137                 303 2 CH.sub.3 i-C.sub.3 H.sub.7                                                                         i-C.sub.3 H.sub.7                                                                           n.sub.D.sup.20 = 1.5189                 304 2 CH.sub.3 i-C.sub.3 H.sub.7                                                                          ##STR401##  n.sub.D.sup.20 = 1.5046                 305 2 i-C.sub.3 H.sub.7                                                                        ##STR402##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5482                 306 2 i-C.sub.3 H.sub.7                                                                        ##STR403##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5414                 307 2 CH.sub.3                                                                                 ##STR404##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5055                 308 2                                                                                 ##STR405##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5184                 309 2 n-C.sub.3 H.sub.7                                                                        ##STR406##                                                                               CH.sub.3     m.p.: 73° C.                     310 2 CH.sub.3                                                                                 ##STR407##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5598                 311 2 CH.sub.3                                                                                 ##STR408##                                                                               n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5248                 312 2 C.sub.2 H.sub.5                                                                         n-C.sub.4 H.sub.9                                                                         n-C.sub.4 H.sub.9                                                                           n.sub.D.sup.20 = 1.5248                 313 2 CH.sub.3                                                                                 ##STR409##                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            m.p.: 98° C.                     314 2 CH.sub.3                                                                                 ##STR410##                                                                               CH.sub.3     m.p.: 87° C.                     315 2                                                                                 ##STR411##         CH.sub.3     n.sub.D.sup.20 = 1.5175                 316 2 C.sub.2 H.sub.5                                                                          ##STR412##                                                                               CH.sub.3     m.p.: 73° C.                     317 2                                                                                 ##STR413##         CH.sub.3     n.sub.D.sup.20 = 1.5338                 318 2 CH.sub.3 CH.sub.2 CF.sub.3                                                                         CH.sub.3     m.p.: 123° C.                    319 2 CH.sub.3                                                                                 ##STR414##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5617                 320 2 CH.sub.3                                                                                 ##STR415##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5187                 321 2 OCH.sub.3                                                                                ##STR416##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5096                 322 2                                                                                 ##STR417##         CH.sub.3     m.p.: 80° C.                     323 2 CH(CH.sub.3).sub.2                                                                       ##STR418##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5496                 324 2 CH(CH.sub.3).sub.2                                                                       ##STR419##                                                                               CH.sub.3     m.p.: 74° C.                     325 2 CH(CH.sub.3).sub.2                                                                       ##STR420##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5392                 326 2 CH(CH.sub.3).sub.2                                                                       ##STR421##                                                                               CH.sub.3     m.p.: 105° C.                    327 2 CH(CH.sub.3).sub.2                                                                       ##STR422##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5355                 328 2                                                                                 ##STR423##         CH.sub.3     n.sub.D.sup.20 = 1.5067                 329 2 C.sub.2 H.sub.5                                                                          ##STR424##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5329                 330 2 CH(CH.sub.3).sub.2                                                                       ##STR425##                                                                               CH.sub.3     n.sub.D.sup.20 = 1.5415                 331 2                                                                                 ##STR426##         C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5308                 332 2 CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR427##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5599                 333 2 n-C.sub.4 H.sub.9                                                                        ##STR428##                                                                               C.sub.2 H.sub.5                                                                             n.sub.D.sup.20 = 1.5493                 334 2 C.sub.2 H.sub.5                                                                         n-C.sub.4 H.sub.9                                                                         CHF.sub.2                                            335 2                                                                                 ##STR429##         CHF.sub.2                                            336 2                                                                                 ##STR430##         CHF.sub.2                                            337 2                                                                                 ##STR431##         CHF.sub.2                                            338 2                                                                                 ##STR432##         CHF.sub.2                                            339 2 CH.sub.3                                                                                 ##STR433##                                                                               CHF.sub.2                                            340 2 CH.sub.3                                                                                 ##STR434##                                                                               CHF.sub.2                                            341 2                                                                                 ##STR435##         CHF.sub.2                                            342 2                                                                                 ##STR436##         CHF.sub.2                                            343 2 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                           CHF.sub.2                                            344 2                                                                                 ##STR437##         CHF.sub.2                                            345 2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         CHF.sub.2                                            346 2 C.sub.2 H.sub.5                                                                          ##STR438##                                                                               CHF.sub.2                                            347 2 CH.sub.3                                                                                 ##STR439##                                                                               CHF.sub.2                                            348 2 CH.sub.3                                                                                 ##STR440##                                                                               CHF.sub.2                                            349 2 CH.sub.3                                                                                 ##STR441##                                                                               CHF.sub.2                                            350 2 OCH.sub.3                                                                                ##STR442##                                                                               CHF.sub.2                                            351 2                                                                                 ##STR443##         CHF.sub.2                                            352 2 CH(CH.sub.3).sub.2                                                                       ##STR444##                                                                               CHF.sub.2                                            353 2 CH(CH.sub.3).sub.2                                                                       ##STR445##                                                                               CHF.sub.2                                            354 2 CH(CH.sub.3).sub.2                                                                      OCH(CH.sub.3).sub.2                                                                       CHF.sub.2                                            355 2 CH(CH.sub.3).sub.2                                                                       ##STR446##                                                                               CHF.sub.2                                            356 2 CH(CH.sub.3).sub.2                                                                       ##STR447##                                                                               CHF.sub.2                                            357 2 CH(CH.sub.3).sub.2                                                                       ##STR448##                                                                               CHF.sub.2                                            358 2 CH(CH.sub.3).sub.2                                                                       ##STR449##                                                                               CHF.sub.2                                            359 2 CH(CH.sub.3).sub.2                                                                       ##STR450##                                                                               CHF.sub.2                                            360 2 CH(CH.sub.3).sub.2                                                                       ##STR451##                                                                               CHF.sub.2                                            361 2 CH(CH.sub.3).sub.2                                                                       ##STR452##                                                                               CHF.sub.2                                            362 2 CH(CH.sub.3).sub.2                                                                       ##STR453##                                                                               CHF.sub.2                                            363 2 CH(CH.sub.3).sub.2                                                                       ##STR454##                                                                               CHF.sub.2                                            364 2 CH(CH.sub.3).sub.2                                                                       ##STR455##                                                                               CHF.sub.2                                            365 2 CH(CH.sub.3).sub.2                                                                       ##STR456##                                                                               CHF.sub.2                                            366 2 CH(CH.sub.3).sub.2                                                                       ##STR457##                                                                               CHF.sub.2                                            367 2 CH(CH.sub.3).sub.2                                                                       ##STR458##                                                                               CHF.sub.2                                            368 2 CH(CH.sub.3).sub.2                                                                       ##STR459##                                                                               CHF.sub.2                                            369 2 CH.sub.3                                                                                 ##STR460##                                                                               CHF.sub.2                                            370 2 CH.sub.3                                                                                 ##STR461##                                                                               CHF.sub.2                                            371 2 C.sub.2 H.sub.5                                                                          ##STR462##                                                                               CHF.sub.2                                            372 2 CH.sub.3                                                                                 ##STR463##                                                                               CHF.sub.2                                            373 2 C.sub.2 H.sub.5                                                                          ##STR464##                                                                               CHF.sub.2                                            374 2 CH.sub.3                                                                                 ##STR465##                                                                               CHF.sub.2                                            375 2 n-C.sub.3 H.sub.7                                                                       n-C.sub.3 H.sub.7                                                                         CHF.sub.2                                            376 2                                                                                 ##STR466##         CHF.sub.2                                            377 2                                                                                 ##STR467##         CHF.sub.2                                            378 2                                                                                 ##STR468##         CHF.sub.2                                            379 2 CH.sub.3 n-C.sub.4 H.sub.9                                                                         CHF.sub.2                                            380 2                                                                                 ##STR469##         CHF.sub.2                                            381 2 CH.sub.2 CHCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                       CHF.sub.2                                            __________________________________________________________________________

Starting compounds of the formula (II):

Example (II-1) ##STR470## 148 g (0.73 mol) of 5-chloro-3-methylthio-1,2,4-thiadiazole are dissolved in a mixture comprising 500 ml of methanol and 23 g of concentrated sulphuric acid, and the whole is heated to reflux. 90.6 g (0.8 mol of H₂ O₂) of a 30% aqueous solution of hydrogen peroxide are then added dropwise. The reaction mixture is heated under reflux for 3 hours. It is then concentrated and the residue is shaken with chloroform/water; the organic phase is washed with sodium hydrogen carbonate solution and then with water, dried with sodium sulphate and filtered. The solvent is carefully distilled off from the filtrate under a water pump vacuum.

113 g (85% of theory) of 5-chloro-3-methylsulphinyl-1,2,4-thiadiazole are obtained as a crystalline product with a melting point of 72° C.

The following compounds, for example, may be prepared in analogy with example (II-1):

3-ethylsulphinyl-, 3-n-propyl-sulphinyl-, 3-i-propyl-sulphinyl, 3-n-butyl-sulphinyl-, 3-i-butyl-sulphinyl-, 3-s-butyl-sulphinyl-, 3-benzyl-sulphinyl, 3-(2-chloro-benzyl)-sulphinyl-, 3-(3-chloro-benzyl)-sulphinyl-, 3-(4-chloro-benzyl)-sulphinyl-, 3-(3-trifluoromethyl-benzyl)-sulphinyl and 3-(4-trifluoromethyl-benzyl)-sulphinyl-5-chloro- 1,2,4-thiadiazole.

Example (II-2) ##STR471## 105 g (0.5 mol) of 2,5-bis-ethylthio-1,2,4-thiadiazole and 3.5 g of sodium tungstate are initially introduced into 260 ml of acetic acid, and 475 ml (5.5 mol of H₂ O₂) of a 30% aqueous solution of hydrogen peroxide are added dropwise at 20° C. to 30° C. and within the space of approx. 90 minutes. The reaction mixture is stirred at 20° C. for 5 hours and then slowly diluted with 2.5 litres of water. The product, which has resulted in crystalline form during this procedure, is isolated by filtering it off with suction.

100 g (74% of theory) of 2,5-bis-ethylsulphonyl-1,2,4-thiadiazole are obtained with a melting point of 42° C.

The compounds of the formula (II) which are listed in the following Table 3 may also, for example, be prepared in analogy with Example (II-2). ##STR472##

                                      TABLE 3                                      __________________________________________________________________________     Examples of the compounds of the formula (II)                                  Ex.                             Melting                                        No.                                                                               n R.sup.3     X              point (°C.)                             __________________________________________________________________________     II-3                                                                              2 n-C.sub.3 H.sub.7                                                                          SO.sub.2C.sub.3 H.sub.7 -n                                                                    50                                             II-4                                                                              2 n-C.sub.4 H.sub.9                                                                          SO.sub.2C.sub.4 H.sub.9 -n                                                                    (n.sub.D.sup.20 = 1.5020)                      II-5                                                                              2 CH.sub.2 CH.sub.2OC.sub.2 H.sub.5                                                          SO.sub.2CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                    80                                             II-6                                                                              2 CH.sub.2 CH(CH.sub.3).sub.2                                                                SO.sub.2CH.sub.2 CH(CH.sub.3).sub.2                                                           93                                             II-7                                                                              2                                                                                             ##STR473##    (n.sub.D.sup.20 = 1.4816)                      II-8                                                                              2                                                                                 ##STR474##                                                                                 ##STR475##    150                                            II-9                                                                              2 i-C.sub.3 H.sub.7                                                                          SO.sub.2C.sub.3 H.sub.7 -i                                                                    (n.sub.D.sup.20 = 1.5147)                      __________________________________________________________________________

Application Example:

In the application example which is given below, the following compound is taken for comparison: ##STR476## (disclosed in EP-A 348737/LeA 26031, cf. Example 28). Example A: Pre-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is watered with the preparation of the active compound. In this context, it is expedient to keep the amount of water per unit area constant. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

0%=no effect (like the untreated control)

100%=total distraction

In this test, the compounds according to Preparation Examples 1, 5, 6, 7, 8, 9, 11, 12, 14, 17, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 41 and 42, for example, display a substantially more powerful effect against weeds than does the known compound (A) (cf. Table A) while being very well tolerated by cultivated plants, for example soya bean.

Additional novel active compounds and their rates of application, and the test plants used and the test results, are shown in the following Table B; the example numbers in this table also refer to the above preparation examples given in Table 2.

                                      TABLE A                                      __________________________________________________________________________     Pre-emergence Test/Greenhouse                                                                             Rate of                                                                        application                                         Active compound            (g/ha)                                                                               Cotton                                                                             Lolium                                                                             Panicum                                                                             Poa                                                                               Galinsoga                     __________________________________________________________________________      ##STR477##                250   0   20  0    50 20                             ##STR478##                250   0   90  95   95 95                             ##STR479##                250   0   80  95   90 100                            ##STR480##                250   0   70  80   80 100                            ##STR481##                250   0   50  90   80 100                            ##STR482##                250   0   40  90   70 100                            ##STR483##                250   0   95  100  95 95                             ##STR484##                250   0   95  90   95 100                            ##STR485##                250   0   70  30   70 100                            ##STR486##                250   0   95  90   70 100                            ##STR487##                250   0   90  90   95 100                            ##STR488##                250   10  70  95   80 100                            ##STR489##                250   40  70  95   95 100                            ##STR490##                250   20  80  95   95 100                            ##STR491##                250   0   95  95   100                                                                               95                             ##STR492##                250   0   80  95   100                                                                               95                             ##STR493##                250   20  95  95   100                                                                               95                             ##STR494##                250   0   95  90   100                                                                               95                             ##STR495##                250   0   95  90   95 95                             ##STR496##                250   0   95  90   100                                                                               95                             ##STR497##                250   20  95  95   100                                                                               95                             ##STR498##                250   0   40  90   90 95                             ##STR499##                250   20  95  95   95 95                             ##STR500##                250   0   95  95   95 95                             ##STR501##                250   0   90  95   95 100                            ##STR502##                250   0   95  95   100                                                                               95                             ##STR503##                250   0   90  95   100                                                                               100                            ##STR504##                250   0   40  95   95 95                             ##STR505##                250   20  50  95   95 95                             ##STR506##                250   0   95  95   100                                                                               100                            ##STR507##                250   0   70  95   95 95                             ##STR508##                250   0   95  95   95 100                            ##STR509##                250   0   100 90   95 90                             ##STR510##                250   0   95  50   95 50                            __________________________________________________________________________

                                      TABLE B                                      __________________________________________________________________________     Pre-emergence Test/Greenhouse                                                  Active                                                                              Rate of                                                                   compound                                                                            application                                                               No.  (kg/ha)                                                                              Digitaria                                                                           Echinochloa                                                                          Poa                                                                               Setaria                                                                            Amaranthus                                                                           Galinsoga                                                                           Portulaca                              __________________________________________________________________________      2   500   100  100   100                                                                               100 100   --   100                                     46  500   95   80    80 90  100   70   --                                      49  250   100  80    80 100 80    95   100                                     1   500   100  100   95 100 100   100  100                                     5   500   95   100   100                                                                               100 100   100  100                                     6   500   100  100   95 100 100   100  100                                     7   500   95   100   95 95  80    100  95                                      8   500   100  100   95 90  90    100  100                                     9   500   95   100   80 100 50    100  100                                     11  500   95   100   95 100 95    100  95                                      12  500   95   100   80 95  --    100  --                                      19  250   95   95    80 95  --    100  70                                      14  500   95   100   90 100 100   100  100                                     16  500   95   95    80 70  80    100  100                                     17  500   100  80    95 95  95    100  95                                      20  250   95   95    95 95  95    100  80                                      21  250   95   95    80 95  80    100  --                                      22  500   95   95    100                                                                               95  80    95   100                                     23  500   100  100   100                                                                               95  70    95   100                                     24  500   100  100   100                                                                               100 100   95   100                                     25  500   95   100   100                                                                               95  --    95   --                                      26  500   95   100   100                                                                               95  --    95   --                                      27  500   95   95    100                                                                               95  70    95   95                                      28  500   100  100   100                                                                               100 70    95   100                                     29  500   95   95    90 90  70    95   95                                      30  500   100  95    100                                                                               100 80    95   100                                     31  500   100  100   100                                                                               100 70    95   100                                     32  500   100  95    95 100 70    100  100                                     33  500   100  100   100                                                                               100 100   95   100                                     34  500   100  100   100                                                                               95  95    100  100                                     35  500   100  100   100                                                                               100 95    100  90                                      36  500   100  100   95 100 95    95   100                                     37  500   100  100   100                                                                               100 90    100  100                                     38  500   100  100   100                                                                               100 95    95   100                                     39  500   100  100   100                                                                               100 95    100  100                                     40  500   95   95    95 95  --    --   --                                      41  500   100  100   95 100 --    90   --                                      42  500   95   100   100                                                                               95  --    95   --                                     190  250   100  100   100                                                                               95  95    95   95                                     191  250   95   100   95 95  80    80   60                                     194  500   100  95    100                                                                               100 100   95   100                                    196  250   95   100   100                                                                               100 95    100  95                                      53  250   95   100   95 95  --    95   70                                     198  250   100  100   100                                                                               95  90    100  95                                     199  250   95   100   100                                                                               100 60    95   95                                      55  250   95   100   100                                                                               100 100   90   95                                      56  250   100  100   100                                                                               100 100   95   95                                      57  250   100  100   100                                                                               100 100   100  100                                     58  250   100  100   100                                                                               100 100   95   90                                     201  250   100  100   100                                                                               100 95    95   60                                     203  250   100  100   100                                                                               95  100   95   90                                      75  500   100  95    100                                                                               100 70    95   95                                     207  500   100  100   100                                                                               95  100   95   100                                    208  500   95   100   100                                                                               100 100   95   100                                     78  500   100  100   100                                                                               100 100   100  100                                     79  500   100  100   100                                                                               100 100   100  100                                     80  500   100  100   100                                                                               100 100   100  100                                     87  500   95   50    95 95  80    100  95                                     210  500   95   100   95 100 100   100  95                                     212  500   95   60    95 95  100   100  100                                    213  500   95   90    95 95  100   95   50                                     310  250   100  100   95 95  100   95   95                                     216  250   95   95    100                                                                               100 95    100  100                                    219  250   100  100   100                                                                               95  --    100  100                                    220  250   100  100   100                                                                               100 100   100  100                                    221  250   95   95    100                                                                               100 60    100  95                                     103  250   100  100   100                                                                               100 50    100  100                                    116  250   95   95    100                                                                               100 --    90   --                                     222  250   95   100   100                                                                               95  --    100  70                                     225  250   100  100   100                                                                               100 100   100  100                                    226  250   95   80    100                                                                               100 100   100  100                                    227  250   100  70    100                                                                               95  100   100  100                                    228  250   100  100   100                                                                               100 100   95   100                                    229  250   100  90    80 95  --    95   60                                     230  250   95   95    100                                                                               95  95    60   --                                     235  250   100  95    100                                                                               95  95    95   95                                     236  250   95   80    90 90  --    --   --                                     237  250   95   95    100                                                                               95  95    95   60                                     240  250   100  95    100                                                                               100 90    95   95                                     243  500   100  --    100                                                                               95  100   100  100                                    247  250   100  100   100                                                                               100 100   95   100                                    251  250   100  95    100                                                                               90  100   100  95                                     __________________________________________________________________________ 

We claim:
 1. An alkylsulphinyl- or alkylsulphonyl-1,2,4-thiadiazolyloxyacetamide of the formula ##STR511## in which n represents the numbers 1 or 2,R¹ represents hydrogen or C₁ -C₈ -alkyl (which is optionally substituted by fluorine, chlorine, cyano or C₁ -C₄ -alkoxy), represents C₂ -C₈ -alkenyl (which is optionally substituted by fluorine and/or chlorine), represents C₂ -C₈ -alkinyl or represents benzyl, R² represents C₁ -C₈ -alkyl optionally substituted by fluorine chlorine, cyano or C₁ -C₄ -alkoxy, or C₂ -C₈ -alkenyl optionally substituted by fluorine or chlorine, represents C₂ -C₈ -alkinyl, represents C₃ -C₆ -cycloalkyl optionally substituted by chlorine or C₁ -C₃ -alkyl, represents C₅ - or C₆ -cycloalkenyl, represents benzyl optionally substituted by fluorine, chlorine or C₁ -C₄ -alkyl, represents C₁ -C₈ -alkoxy optionally substituted by C₁ -C₄ -alkoxy, or represents C₃ -C₄ -alkenyloxy, or R¹ and R², together with the nitrogen atom to which they are bonded, form a saturated or unsaturated, five- to seven-membered nitrogen heterocycle which is optionally substituted once to three times by C₁ -C₃ -alkyl and which is optionally benzo fused, and R³ represents C₂ -C₄ -alkyl optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy, dioxolanyl or dioxanyl or represents phenyl or phenyl-C₁ -C₂ -alkyl which are in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy.
 2. An alkylsulphinyl- or alkylsulphonyl-1,2,4-thiadiazolyloxyacetamide according to claim 1, in whichn represents the numbers 1 or 2, R¹ represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or n-, i- or s-pentyl which are in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, or represents propenyl, butenyl, propinyl or butinyl, R² represents methyl, ethyl, n- or i-propyl, n-, i or s-butyl, n-, i- or s-pentyl, or n-, i- or s-hexyl which are in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, represents propenyl, butenyl, pentenyl, propinyl, butinyl or pentinyl, represents cyclopentyl or cyclohexyl which are in each case optionally substituted by methyl or ethyl, represents cyclohexenyl, represents benzyl which is optionally substituted by fluorine, chlorine or methyl, or represents methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, or n-, i- or s-pentyloxy which are in each case optionally substituted by methoxy or ethoxy, or R¹ and R², together with the nitrogen atom to which they are bonded, represent piperidinyl which is optionally substituted one to three times by methyl and/or ethyl, represent pyrrolidinyl which is optionally substituted once or twice by methyl or ethyl, represent perhydroazepinyl or represent 1,2,3,4-tetrahydro(iso)quinolinyl, and R³ represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl which are in each case optionally substituted by fluorine, chlorine, -cyano, methoxy or ethoxy or represents phenyl or benzyl which are in each case optionally substituted by fluorine, chlorine, cyano, methyl or methoxy.
 3. A herbicidal composition which comprises an effective amount of a compound according to claim 1 and an inert carrier.
 4. A process for controlling weeds which comprises applying a compound according to claim 1 to said weeds or to a habitat in which they reside.
 5. A process for preparing alkylsulphinyl- and alkylsulphonyl-1,2,4-thiadiazolyloxyacetamides of the formula (I) according to claim 1, which comprises reacting(a) 1,2,4-thiadiazole derivatives of the general formula (II) ##STR512## in which X represents halogen or the grouping --S(O)_(n) --R³, andn and R³ have the meaning given in claim 1, with hydroxyacetamides of the general formula (III) ##STR513## in which R¹ and R² have the meaning given in claim 1,where appropriate in the presence of a diluent, where appropriate in the presence of an acid-binding agent and where appropriate in the presence of a catalyst, or in that (b) alkyl(aryl-, aralkyl-)thio-1,2,4-thiadiazolyloxyacetamides of the general formula (IV) ##STR514## in which R¹, R² and R³ have the meaning given in claim 1,are reacted with an oxidizing agent, where appropriate in the presence of a catalyst and where appropriate in the presence of a diluent.
 6. A 1,2,4-thiadiazole derivative of the formula ##STR515## in which X represents halogen or the grouping --S(O)_(n) --R³,n represents the numbers 1 or 2, and R³ represents C₂ -C₈ -alkyl optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy, dioxolanyl or dioxanyl or represents phenyl-C₁ -C₂ -alkyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy. 